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House holiday rentals in Chesterfield

Find and book unique houses on Airbnb

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Popular amenities for Chesterfield house rentals

House rentals with a pool

Superhost
Home in Doncaster
4.94 out of 5 average rating, 94 reviews

Large Modern Décor 3 Bed with Driveway & Garden

Christopher JohnRating, 5 stars4 months ago
Lovely cosy house which was clean and tidy. This was our second stay at Homestead and we will be coming back.
Home in Derbyshire
4.75 out of 5 average rating, 4 reviews

Ashbourne Cottage near Dovedale

JackRating, 5 stars2 months ago
Really good place stay, easy to find. Had a great time!
Home in Bakewell
4.7 out of 5 average rating, 10 reviews

Love Nest - an intimate hideaway

DanielRating, 5 stars24 months ago
our stay at staycation cottages in bakewell was lovely. the love nest Lodge was very quaint and well equipped. the bathroom was especially layed out nicely. I enjoyed the access to the football playing area, pool area and the swimming pool. we used the bbq area once and made full use of the boot room for leaflets and information for our stay would definitely return back
Superhost
Home in Hepworth

Grove Farm Cottage

ChloeRating, 5 stars1 month ago
Lovely stay, the farm was beautiful and the animal feeding was the highlight of our childrens’ stay. Pool was great, super clean everywhere, and they provided maps of local walks which we utilised too. Couldn’t have asked for much more.
Guest favourite
Home in Alport
4.95 out of 5 average rating, 21 reviews

Peak District Manor: Pool + Hot Tub + Fire Pit

StephanieRating, 5 stars2 months ago
The house was absolutely incredible and excellent value for money. It was in stunning surroundings, the hot tub was amazing and the exclusive booking system for use of the pool was a lovely addition. The house was spotless and full of character and the private garden was also wonderful. The beds were really comfortable and there was just the right balance of charm, space and comfort. We definitely struck gold when booking this gem. Thanks so much for all of your support in making this a trip to remember!
Home in Buxton
4.86 out of 5 average rating, 7 reviews

The Manor House

EiraRating, 5 stars38 months ago
What a wonderful stay at Manor Farm. The house was beautiful, well maintained, extremely spacious and very comfortable. The surrounding countryside was stunning, with great food being served in nearby pubs and plenty of places to visit. Great space for youngsters too, with the wildlife - baby rabbits, sheep and birds and of course the swimming pool and games room, all of which they loved. Thanks to the hosts for their welcome and hospitable atmosphere.
Home in Buxton
4.64 out of 5 average rating, 11 reviews

Badgers Wood

JackRating, 5 stars46 months ago
Great value for money. Can't stress enough how friendly and reliable the staff were. We had a lovely week stay, the house was clean, the beds were comfy and the scenery was perfect. We were informed of the booking system for the swimming pool and games room, so you could have the room to yourself which was great. The pool was clean, the games room was kept tidy and the house surroundings were really lovely to walk around. You can tell the grounds were well maintained and kept in good shape as the workers never stopped, but were always so friendly. This property is perfect for bike riders, walkers and pub crawlers. You couldn't get bored.
Home in Derbyshire
4.75 out of 5 average rating, 4 reviews

Pippinwell

DemiRating, 5 stars15 months ago
Me and my family really enjoyed our stay! The place was clean and there was plenty of space for all 8 of us (and our dog!). The area is stunning, very quiet with plenty of nice walks. The pool/games room area is shared with the other cottages, which wasn't made clear when booking. We thought it was part of our cottage, which we were slightly disappointed to find out this wasn't the case. However, overall we'd still consider staying here again!

Weekly house rentals

Guest favourite
Home in Eckington
4.88 out of 5 average rating, 41 reviews

Lovely house Eckington Sheffield

LilyRating, 5 stars2 weeks ago
Lovely clean and cosy house. Great communication
Top Guest favourite
Home in Derbyshire
4.99 out of 5 average rating, 265 reviews

Chert Cottage, Great Longstone, Bakewell Peak Dist

AndrewRating, 5 stars2 weeks ago
We had a lovely, long weekend stay at Chert cottage. Great Longstone is an excellent location, with several pubs within walking distance. Beautiful scenery is on the doorstep, with places like Bakewell and Buxton a short drive away. Sarah was an excellent host - she was very responsive and we really appreciated the cake, milk and flowers on arrival. Chert cottage itself was great - very clean and equipped with everything you could possibly need - we particularly loved sitting out in the garden in the evening! Many thanks Sarah, we had a great time.
Guest favourite
Home in Bolsover
4.86 out of 5 average rating, 58 reviews

The Cottage - Derbyshire

KatieRating, 5 stars1 week ago
We (3 friends) had a really nice stay here. The house was very clean and well looked after and the views from the front of the house just amazing. Comfy beds, plenty of parking and the kitchen had everything we needed. Great location too for our visits to Bolsover Castle and Renishaw gardens.
Top Guest favourite
Home in Derbyshire
4.99 out of 5 average rating, 151 reviews

Highfield House - Rural Retreat Derbyshire

KimRating, 5 stars1 week ago
A wonderful house in a quiet location. Lovely pubs and country walks on your doorstep! Hot tub a great bonus, ideal for our reunion weekend. Thank you Penny... perfect :-)
Guest favourite
Home in Derbyshire
4.97 out of 5 average rating, 29 reviews

Cosy 2 bed home CHESTERFIELD

KatieRating, 5 stars4 months ago
Me and my partner visited over Valentines weekend and were so pleased with the accommodation, it was easy to find and located in a lovely town with lots of pubs and takeaway options. Everything from the decor and furniture to the facilities available were brilliant, the house was spotless and we couldn’t find a single thing to complain about. Thoroughly enjoyed our stay and would happily return in the future x
Top Guest favourite
Home in Castleton
4.93 out of 5 average rating, 909 reviews

Riverbank Cottage - Annex

FraserRating, 5 stars2 weeks ago
Booked this trip last minute and was not disappointed with our choice, the instructions for parking and how to find the cottage was spot on. Less then a couple minutes walk and you’re at all the coffee shops and pubs with a short drive to other villages and all the famous walks.
Top Guest favourite
Home in Brimington
5 out of 5 average rating, 16 reviews

Blissful Barry’s

HarrietRating, 5 stars1 month ago
A comfortable and well appointed Airbnb in a lovely peaceful area. Host was always quick to respond to any questions and the whole process was easy and efficient. Would definitely recommend to anyone looking to stay near Chesterfield but in a more relaxed area!
Superhost
Home in Derbyshire
4.69 out of 5 average rating, 87 reviews

Commuters Getaway Chesterfield

LesleyRating, 5 stars4 weeks ago
we have just spent 5 days there would recommend it.Dan was very helpful .The house is very central for exploring the Peak District and is a nice walk into Chesterfield about 20 minutes, plenty of pubs to choose for meals .

Private house rentals

Guest favourite
Home in Derbyshire
4.98 out of 5 average rating, 49 reviews

Luxury manor house with hot tub

NiccolaRating, 5 stars5 days ago
We loved our stay at Gill and Steve’s. It’s one of the nicest we have ever stayed in. My husband and I plus 8 of our friends stayed for two nights. We had so much fun!!! The outside space is perfect for dinners and drinks. The house is huge and has everything we needed. Gill and Steve are amazing hosts. Such good people and were so responsive and helped us to make a lovely weekend for our friends. Enough parking for all 5 couples to drive!! Will be back!! :)
Superhost
Home in Mosborough
5 out of 5 average rating, 9 reviews

Detached Converted Farmhouse, Mosborough, S20

LisaRating, 5 stars10 months ago
A beautiful house, and a great host. The property was just like the description and photos. Great for us as we have family close by. Dean was brilliant at keeping in touch and came back whenever I messaged him. Will certainly book again. Thank you for an amazing stay.
Guest favourite
Home in Cutthorpe
5 out of 5 average rating, 22 reviews

Elegant and exclusive Manor House stay, Derbyshire

AryanRating, 5 stars3 weeks ago
We had an absolutely wonderful stay at Salli’s place. The house itself is stunning, spacious, beautifully decorated, and equipped with everything we needed for a comfortable and relaxing trip. It’s also perfectly located, with easy access to some fantastic hiking trails nearby, which we really enjoyed exploring. Salli was an excellent host—friendly, responsive, and incredibly helpful throughout our stay, making sure we had everything we needed. We would highly recommend this property to anyone looking for a peaceful getaway in a beautiful setting. Thank you, Salli, for hosting us!
Top Guest favourite
Home in Derbyshire
5 out of 5 average rating, 17 reviews

1 Bedroom Terrace in Quiet area

ShivRating, 5 stars2 weeks ago
I stayed at Sams place for almost two months and it was one of the best decisions ever. The house is very well done and in a very nice and safe location. It is close to bus stops and the royal hospital. Sam replied almost immediately if I had any questions or doubts. The house is spacious and with a very nice backyard as well. I'm glad I could this place a home for 2 months. I would highly recommend Sams place for anyone looking to stay in Chesterfield for short/long term.
Top Guest favourite
Home in Tansley
4.96 out of 5 average rating, 69 reviews

Fox Cottage at Yew Tree Farm

PaulRating, 5 stars1 day ago
A very nice cottage in an excellent location. Very clean with all amenities included. Lots of attractions very close by. Highly recommended Homemade jam much appreciated We really enjoyed our stay!
Guest favourite
Home in Derbyshire
4.92 out of 5 average rating, 73 reviews

Lovely 3 Bedroom house - great location

LyndaRating, 5 stars5 months ago
We used this lovely home while waiting for the purchase of our new home to complete, we wanted somewhere in Chesterfield that was going to feel like a home and be comfortable while I’m undergoing chemo, Winston’s home ticked every box and our 2 dogs and 2 house cats definitely approved, the garden is secure and safe, parking outside was perfect, we couldn’t have picked a better property, even suppling a Christmas tree and decorations made it that much more special, thank you 🙏
Guest favourite
Home in Clowne
4.93 out of 5 average rating, 76 reviews

Lily's Cottage

LisaRating, 5 stars2 weeks ago
Great house with everything we needed. Great value
Top Guest favourite
Home in Derbyshire
5 out of 5 average rating, 47 reviews

Hugo’s Luxury Barn

JennyRating, 5 stars1 day ago
This place is truly beautiful the surroundings are incredible the place is beautiful, garden was lovely and the barn was perfect I would definilty recommend and it was amazing value for money

Quick stats about house rentals in Chesterfield

  • Total rentals

    60 properties

  • Nightly prices starting at

    $50 NZD before taxes and fees

  • Total number of reviews

    3.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield
  6. House rentals